Development of tartaric acid derived chiral guanidines and their application to catalytic enantioselective α-hydroxylation of ß-dicarbonyl compounds.

ABSTRACT

A novel library of chiral guanidines featuring a tartaric acid skeleton was developed from diethyl l-tartrate. These guanidines are easily accessed with tunable steric and electronic properties. The utilities of the guanidines were highlighted by their ability to catalyze the α-hydroxylation of ß-ketoesters and ß-diketones with remarkable efficiency and excellent enantioselectivity.